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Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 55 Cottages in Westport with updated reviews, rates, and availability.

Adorable 1-Bedroom Cottage in Weston, CT
Fridge, microwave, oven, stovetop

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (40)
"beautiful cottage with all the amenities you need.. charming historic property.. would highly recommend "
The price is AED 716
AED 1,114 total
includes taxes & fees
5 Jun - 6 Jun
Adorable 1-Bedroom Cottage in Weston, CT
Cozy Cabin @ Sticks & Stones Farm
Interior

Cozy Cabin @ Sticks & Stones Farm

8.4 out of 10, Very Good, (6)
"This property was just what we needed when visiting the area. The rustic but peaceful setting is one we wish we could have enjoyed more of. We would have loved to have spent more time on property with a fire in the wood stove or relaxing by the brook out back. The mattresses were comfortable and we slept well. "
The price is AED 349
AED 702 total
includes taxes & fees
5 Jun - 6 Jun
Cozy Cabin @ Sticks & Stones Farm
Beachfront cottage located in the heart of Fairfield Beach!!
On the beach

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Beachfront Connecticut Retreat w/ Views!
On the beach

Beachfront Connecticut Retreat w/ Views!

9.6 out of 10, Exceptional, (7)
"Just a wonderful beach cottage in a great spot that had all we needed"
Beachfront Connecticut Retreat w/ Views!
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Fridge, microwave, stovetop, dishwasher

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

7.8 out of 10, Good, (6)
"We felt very cozy in the home. We were comfortable letting our dogs run around the back yard. Excellent location to all our favorite places. We will stay again. "
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths
Interior

A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths

2.0 star property
10.0 out of 10, Exceptional, (2)
"The pictures do not do this cottage justice. The Christmas decorations were a great surprise too. Plenty of room for all 8 of us with everything we need nearby. "
A Hidden Gem! Cozy Cottage with huge Pool & Garden! 8 guest - 4 bedrooms-2 baths
Second floor cottage apartment located in a private community.
Miscellaneous

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (10)
"We really enjoyed this place and location. Everything as advertised. Clean, safe area with great parking, convenient to 95 and all of Stamford, comfortable bed, W/D steps away. "
Trendy 1 bedroom +loft apartment w/ parking
Beach house cottage steps to private beach in the heart of Bayville
Interior

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (9)
"Very cute house within walking distance to the beach and restaurants. Great place to stay when we visited daughter at LIU!"
Beach house cottage steps to private beach in the heart of Bayville
Beach cottage on private beach!
Beach nearby, sun loungers, beach towels

Beach cottage on private beach!

10.0 out of 10, Exceptional, (4)
"It was a very nice cottage. Great price for staying right on the beach"
Beach cottage on private beach!
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Terrace/patio

Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

9.0 out of 10, Wonderful, (7)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC
Streamside Cottage @ Sticks & Stones Farm
Miscellaneous

Streamside Cottage @ Sticks & Stones Farm

The price is AED 626
AED 1,122 total
includes taxes & fees
18 Jun - 19 Jun
Streamside Cottage @ Sticks & Stones Farm
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (86)
"Had the best time. Walked to the beach. Great local restaurants as well."
Westport "Gold Coast" across from Southport beach
Renovated Milford Beach home by Charles Island/Silver Sands Pk
Beach nearby

Renovated Milford Beach home by Charles Island/Silver Sands Pk

10.0 out of 10, Exceptional, (4)
"This place was perfection for my mom and I. The location was easy to get to from highway, the inside of the place was spotless, updated and cozy and property owner Susana was highly responsive to any questions we had. The location was ideal for walks both on the beach and on walking paths. We will definitely stay again in the future. "
Renovated Milford Beach home by Charles Island/Silver Sands Pk
South Salem Vacation Rental w/ Furnished Deck!
Miscellaneous

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Charming 3 Bedroom Beach Front Cottage
Outdoor dining

Charming 3 Bedroom Beach Front Cottage

2.0 star property
10.0 out of 10, Exceptional, (3)
"Stayed here while attending the Soundside Fest. Perfect location to be away from the busy Bridgeport area. The water is right there and it’s the perfect space for a weekend get away."
Charming 3 Bedroom Beach Front Cottage
Bright Milford Beach House w/ Outdoor Shower
Interior

Bright Milford Beach House w/ Outdoor Shower

3.0 star property
Bright Milford Beach House w/ Outdoor Shower
Cozy Riverside Cottage
Outdoor dining

Cozy Riverside Cottage

10.0 out of 10, Exceptional, (3)
"Check-in was very simple. The neighborhood very quiet and walkable along the bay. All the amenities were available plus extras. The host was super and always reachable, much appreciated. We plan on staying again soon!!"
Cozy Riverside Cottage
Beachfront Connecticut Retreat w/ Views!
Beach towels, snorkeling

Beachfront Connecticut Retreat w/ Views!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great spot on the ocean with an amazing host!"
Beachfront Connecticut Retreat w/ Views!
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

How much do cottages in Westport cost?
You’ll pay between AED 349 and AED 716 per night for cottages in Westport. Whatever your budget, the perfect stay is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your cottage in Westport with Expedia?
Reserving a cottage in Westport is as easy as working out your travel dates and selecting your ideal place for outdoor relaxation and recreation. From upscale retreats to affordable properties and cottages that feature perks like a hot tub, Expedia has something for all traveler tastes. As for the best deals around? We’ve got you covered!
How can I find cheap cottages in Westport?
With Expedia’s handy filter tool, getting your hands on cheap cottages in Westport has never been easier. To discover accommodations that’ll make your bank balance smile, narrow your search results by budget, amenities and star rating.